


Coooooooooooooooooool!

by DraceDomino



Category: Pocket Monsters | Pokemon (Anime)
Genre: Anal Sex, Bukkake, Cock Slut, Cool, Crossdressing, Cumplay, Feminization, Gangbang, M/M, Oral Sex, Panties, Prostitution, Schoolgirls, Small Penis, Spitroasting, Uniforms
Language: English
Status: Completed
Published: 2019-03-09
Updated: 2019-03-09
Packaged: 2019-11-14 05:21:05
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,510
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/18046259
Author URL: https://archiveofourown.org/users/DraceDomino/pseuds/DraceDomino
Summary: How did Team Rocket get the tickets to the S.S. Anne in order to lure Ash and his friends into a trap?Jessie whored James out to a bunch of guys behind the bushes. It was easy, considering they already had the schoolgirl costumes!





	Coooooooooooooooooool!

Coooooooooooooooooool!  
-by Drace Domino

“But Jessie, why do I have to be that one that does this?!” James’ voice was as whiny as ever, and his lower lip trembled as his partner shoved him into the bushes. The two had just finished donning the outfits needed for their latest scheme to nab Pikachu, a pair of schoolgirl uniforms that fit each one of them perfectly. It was a bit surprising in James’ case - the pleated skirt showed off a pair of smooth legs and the tight fitting sweater vest gave him the angles of a flat-chested young woman. Not much needed to be done with his already soft and silky hair aside from a quick dose of blonde color, and the faint pink lipstick made even his whimpering mouth look pretty. “I...I wouldn’t even be able to handle as many customers as you!”

“You’re the one that wasted all of our money on that stupid Magikarp!” Jessie’s response was immediate, she had been waiting for a good reason to throw that blame. As James continued to dig his heels in the dirt to resist being shoved into the bushes, Jessie simply kept strong arming him in a clear display of which of the two of them was tougher. “If we’re going to lure those twerps onto the S.S. Anne, we need to get them tickets, and it’s your fault we can’t afford them! So get back there and wait for your customers to come around, or I’ll give you a worse pounding than they do!”

James made one last gasping noise as Jessie rammed him with her shoulder, launching the crossdressing young man into the bushes beyond. It was the thickest set of them Team Rocket could find in town - the perfect cover for the job that needed to be done. Under normal circumstances, Team Rocket would’ve just stolen the money they needed to get the tickets, but this was too good an opportunity. They couldn’t risk getting caught by Officer Jenny for trying to mug a couple of tourists, not when there was a better way to make the cash so easily at hand.

Besides, as Jessie gazed over her shoulder to the bushes where James waited, she couldn’t help but smile broad from ear to ear. This would be a fine punishment for James wasting all their money on that useless fish!

 

“Hey, dudes, like, how are you?!” Jessie giggled as she bounced before a group of three men - older tourists, likely there to get onboard the S.S. Anne itself. As she hopped in front of the trio her schoolgirl skirt danced around her thighs and her breasts bounced neatly in her sweater, ensuring that the eyes of all three were locked against her. Leaning heavily on a ludicrous valley girl voice, the most cunning of the Team Rocket trio gazed at the men with a look of joyful enthusiasm. “Are you going on that totally cool boat?! Like, it doesn’t leave for another few hours, so maybe you’d like to have some totally radical fun beforehand!”

The men all blinked - accosted in the middle of broad daylight by a bouncing schoolgirl, one that was already moving a hand out to tease fingers across one of their chests. The three men all had a distinguished look to them, well-dressed with finely styled hair. Professionals that were looking to relax during their break, which naturally meant they weren’t at all unaccustomed to this sort of offer. The center of the men arched a brow at the offer, and took the time to look Jessie up and down with a hungry, smirking gaze.

“What did I tell you, boys?” He nudged his pair of friends, and beamed. “You come down to the docks, and the whores come out of the woodwork.”

“She’s a cute one, too!” One of the other men chimed up, before stepping closer towards the schoolgirl that had approached them. “Hey sweetie, think you can handle all three of us at on--”

The man’s advance upon Jessie only lasted as far as him touching the hem of her skirt. He learned in swift fashion that she was a girl to admire from a distance, as she locked her hand around his wrist and suddenly wrenched it back, making him give a sharp cry of pain. The Team Rocket girl’s expression changed dramatically and the valley girl tone dropped immediately from her voice, her temper flaring as she roared at the trio.

“Do I look like I’m that kind of girl?!” She flared, fire in her eyes and venom lashing out from every last word. “Give me your wallets, you miserable creeps!”

...okay. So it was still mostly a mugging. But at least they weren’t going to leave empty-handed.

***

The visiting men really should’ve reported to Officer Jenny that an angry valley girl took their wallets and shoved them into the bushes - but when they arrived in the small clearing beyond them they realized that her offer wasn’t totally insincere. They indeed were going to get to have some fun in return for the money they had lost, but it wasn’t with the hot-tempered girl with ludicrous hair that had just accosted them.

It was with her very cute, very feminine, and very eager friend waiting for them.

“Like, hiiiiiiiiiiii~” James had already gotten into character, greeting the three stumbling men with a playful smile spread across his pink lipstick. In the same manner of scandalous schoolgirl outfit as Jessie, he bounced towards the three, held his hands to his chin, and wobbled back and forth from the waist. “Are you three going to fuck me? Coooooooooool!”

The tourists stared, exchanged cautious glances. The past few minutes had been a schoolgirl-filled blur, and although their wallets had just been bullied away from them the compensation they were about to receive was tremendous. The new blonde schoolgirl giggled vapidly as she swung her hips from side to side, allowing the pleats of his skirt to dance back and forth across beautifully soft, smooth thighs, doing his best to tempt the men into taking what they paid for. He had put up a bit of a fight, but James was clearly giving his all to the job. A real trooper, that one.

“Heh...all right, guys, we might as well.” One of the tourists spoke to his friends, and stepped forward to the new cute girl they were offered. He pressed a hand to James’ shoulder and started to push, maneuvering the young man straight down to his knees in their little spot of privacy through the bushes. There wasn’t any resistance as James dropped, and indeed he even moved his hands forward to press against the growing bulge pressing against the tourist’s pants. While his cock was slowly worked free by the fledgling whore the man let his hand drop down to James’ hair, threading fingers through the soft blonde locks and giving a slow groan of pleasure once he felt his zipper pulled down to the bottom. “Glad you’re friendlier. That little friend of yours is a real bitch, you know.”

“Oh, tell me about it!” James blurted out, dropping into his real voice for a moment and gazing up at the stunned older man. “She’s the bossiest person I know! She’s even bossier than my actual boss! The stories I could tell y--” His eyes lifted as he realized just what he was doing, and a blush rapidly crossed his face. All three of the men were giving James a curious look from the sudden outburst in a masculine voice, and the Team Rocket boy quickly spoke up to do some damage control. “Er...I mean...coooooooool!”

“...this chick’s really fucking hot, guys.” Was the only observation that any of them made as the other two men stepped forward, all of them working to help pull their cocks free. James was bubbling and smiling as the three tourists all unslung their lengths - each one of them an impressive mouthful that put what James had tucked into his panties to shame. As they flopped forward to smear against his cheeks and drape within his open palms the young man giggled and cooed in that silly valley bimbo voice, turning his head from side to side to give their dicks a tiny lick. Before long he had wrapped his palms around two of those impressive lengths while the first man guided his tip to James’ mouth - lining it up right against that light pink lipstick and preparing to shove it straight inside.

“All right, honey,” He smirked, and threaded his fingers into James’ blonde hair, pushing forward just enough so that James’ lips crowned around the very tip. “After how your friend acted, we’re not gonna be gentle. Hope you’re ready for that!”

In response, James simply lifted his front two fingers on both hands - offering double peace signs while the rest of his grip was still wrapped around those two thick, throbbing cocks. His eyes closed in a chipper state and his voice slipped out once more, a sound that was soon muffled as the tourist shoved forward to lodge his cock deep against the young man’s tongue.

“Cooooooooo--mmmphh!” James’ valley girl cry was cut off by a muffled moan, and the boy convulsed in place as he was suddenly forced to deepthroat the tourist. The man in charge wasn’t lying, after Jessie had mugged them they were going to be damn sure to take it out on the hot little piece they were offered in return. As the tip of his cock ran across James’ tongue and straight down his throat, the Team Rocket boy fought his gagging reflex so he could keep handling that impressive member all the way down to the base. His nose pressed against the button of the tourist’s jeans and all the while the other two were having their own bit of fun, swinging their dicks back and forth and letting those precum-glistened cockheads slap against his cheeks.

“Ha! Choke on it, you little whore!” One of the men chimed up, grinning as he pointed just below James’ chin. “Look at that! You’re making her throat bulge! She’s a real cocksucking champ.”

“Don’t take too long, I want my turn, too!” Another of them spoke, but wasn’t merely content with just cockslapping James while his friend had his fun. He soon crouched down to James’ level and moved a hand up and across the young man’s sweater vest, caressing where his flat schoolgirl tits were against the fabric. Smooth and flat but nonetheless sensitive, James’ joyful gagging noises continued as the man managed to zero in on his nipples through the fabric and gave them a few hard, sudden twists. “Flat-chested little slut. Let’s see what she’s got going on under here…”

James wasn’t in any position to resist, and in fact he even moved to help them. His hands dropped down to the edges of his pleated skirt, pulling it up in dainty and feminine fashion to show that just underneath there was a pair of soft pink panties - complete with a tiny little package stuffed within. Hardly something to brag about and in fact hardly a comparison to any of them, but it was still quite clear - this schoolgirl was packing something extra.

Once again, the men reacted in pure enthusiasm.

“Oh...am I gonna enjoy fucking her.” The kneeling man murmured, and stretched a hand out to help himself to a few grasps and grabs. His fingers moved up and down James’ smooth, pale thighs in teasing fashion and made it openly difficult for the boy to focus - so much so that James’ voice gave a staggered grunt as that enormous cock wedged a little deeper in his mouth. By that point the tourist filling his mouth was leaning forward with all his weight, refusing to let James up for a simple gasp of breath and absolutely determined to smear every dot of pale pink lipstick off at the base of his dick. James, for his part, absolutely relished it. Twitching and whimpering, the Team Rocket boy was a quivering mass of pleasure as he was forced to deepthroat that impressive girth, and his sensitive delight flared all the more as a hand moved out to grasp at that tiny coin purse nestled between his thighs. A hungry, possessive grip, squeezing his small package and even pressing the two center fingers against him through the fabric of the panties, just as if he was fingering a pussy.

“Yeah...she’s fucking perfect.” The man groping James cooed, his voice hot and practically at the edge of his throat. He wasn’t willing to resist much longer, and thankfully he wouldn’t have to. As James’ coin purse was fondled and designs were made on his ass, the Team Rocket boy finally started to pull his head back up from the base of that penetrating, thick length. As it flowed from his throat and past his lips he was left openly gasping - ribbons of spit dangling from the corners of his lips and a heavy blush rushing over his cheeks. The three men all gazed down at him down with one of their cocks coated in his saliva, and yet James knew that it wasn’t going to be enough. To that end, he slipped a hand down to a pocket within his sweater vest and pulled out a tiny bottle of lube - the perfect accessory to a gangbang in the bushes.

“Like, now we can have all the fun we want, hehehehehe!” His flirty and silly tone continued, complete with the natural catchphrase. “Coooooooool~”

Cool indeed.

***

Past the tall line of bushes near the S.S. Anne, the three tourists were tearing into James while the young man was still firmly within his glorious, sexy schoolgirl outfit. The bottle of lube laid empty on the floor and in short order all three of them had their chance to slip inside of him, making good use dividing his two holes between three separate men. The leader of the group had taken James’ ass first - pushing him to his hands and knees in the dirt, lifting his schoolgirl skirt and pulling his panties down just enough to give him access to the tight, tender pucker of his ass. When the other two men knelt in front of them with their own cocks exposed James was tasked with sucking them both off in equal measure - pumping their dicks when he was able and slathering them in ribbons of spit that connected all three of them in a slippery triangle of dew.

Hidden within the bushes, the three men greedily spitroasted the Team Rocket boy while thoroughly appreciating his feminine, schoolgirl style. Hands flowed within his silky hair with appreciative delight, fingers passed over his flat chest and pinched his nipples fiercely through the sweater, and from time to time they even reached down to grasp his little package through the panties and give him another two-finger press as if they were sinking knuckle-deep into a warm, wet little cunt. They were aggressive, they were hungry for his holes, and they weren’t in any mood to fuck around with asking if it was too hard.

It wasn’t. In fact, though while James’ valley girl voice and his ditzy performance were purely for show, his desperate moaning and gleeful delight wasn’t. The roll of his hips into their touch was entirely genuine, as was the trembling in his thighs when he wedged back against their laps and took every inch of rock hard cock deep inside of his ass. He was an eager little schoolgirl slut that sunny afternoon, and the fact that it was the thing that got them the money for the S.S. Anne tickets made it all the better. When the first of the men thrust forward and released his spunk within James’ ass the young man quivered in glee, his mouth pressed to the lap of another with a pulsing length bulging his throat. He barely had time to relish the creampie before there was a loud popping noise as his new friend pulled free, only to spank his ass to the side and offer it up to the next.

Another cock was pressed against his creamy center and pushed forward with the same recklessness, driving James’ knees into the dirt and lunging forward again and again to plunge into that already overflowing hole. There was no respite for the Team Rocket boy as the cock he was sucking was pulled free only so he could clean off the one that had just finished in his ass - a method that would soon become routine as the men continued to use him. Load after load James was filled with cum behind the bushes, some of it offered against his tongue hiding behind those faded pink lips, and some of it deposited squarely in his core.

When the men neared the end of their time with their schoolgirl slut, a trembling James stood before them with one hand lifting his pleated schoolgirl skirt and the other hanging a thumb against the waistband of his panties - pulling them open just so the men could all see the tiny, glistening coin purse hiding within.

Well...so they could see it, and aim for it. For the finale of James’ whorish afternoon the men all stood in a semi-circle around their schoolgirl slut, each one of them with their hands locked against their cocks as they pumped fiercely and fast against their members. Two of them rested powerful hands on James’ shoulders as they all aimed their tips downward, pointing squarely at the trembling, small length that had remained soft and tender the entire time. The Team Rocket boy had been flaccid the entire time he was pounded and forced to deepthroat cock after cock, but that didn’t mean he wasn’t excited - in fact, by the marks of cum patting against the inside of his panties, he had been leaking dots of cream ever since they had begun.

“Ohhh, like, this is totally the most fun I’ve ever had!” James’ girlish voice was partially fading now, the result of his throat strained not only from moaning but from the cocks that had battered it from within. He even trembled on his knees as he braced himself, the back of his panties becoming rapidly damp as the cum he had been flooded with oozed out bit by glorious bit. His eyes were shining and those faded pink lips were smiling broadly as he exposed his tiny package, which even twitched to a state of half-stiff excitement as it prepared for its bath. “This is going to feel so...so...cooooooooooool~”

One last time, before the men all finished up. James shuddered in pleasure as they began to unload, all three cocks releasing their spunk at around the same time and all of them firing against that tiny length. Within the bath of cum that slathered his coin purse James’ body responded in kind, dribbling a bit more of his own spunk that was soon lost in the mess. Those soft pink panties were painted with white from within, soon soaking against the fabric and seeping out from in between the seam pressed to his flesh, oozing across smooth thighs from the front just the same as they were from the back. The men shuddered and groaned as they unleashed their final torrent for the afternoon, covering James to the point that his little cock outright disappeared underneath the bath, vanishing below the surface of white where it convulsed and dribbled and leaked.

“Heh. That’s it for me, thanks for the fun, slut!” The lead man beamed as he put his cock away, and took one last glance at the creamy mess they had made of the schoolgirl’s panties. The others soon followed suit, leaving James behind as a dripping, well-filled whore that would have the taste of cock on his tongue for hours to come. “I’d give you a tip, but...well, your bitch friend made sure that isn’t going to happen!”

“Ohhh, that’s all right, this was so cooooooooooooool!” James giggled sweetly, releasing the waistband of his panties and letting his skirt fall down around his thighs once more. It was a glorious, sticky bath that coated his cock and filled him with a profound warmth, and he practically melted on the spot as the men all started to leave. He raised a hand and waved to see them off, giggling wildly and femininely as he did so. “Bye, thanks for good time, boys!”

He’d be leaking cum for hours. His panties would be sticky, and cum would slowly ooze down the entirely of his legs until meeting the edge of his knee high schoolgirl socks. He was a dirty, cum-coated, assfucked mess...and couldn’t be any happier for the fact.

Jessie’s plan to score them S.S. Anne tickets was really, really, really co-

Awesome. It was an awesome fucking plan.

The End.

**Author's Note:**

> I saw this episode the other day and instantly knew I HAD to write a story to match it. And some feminized James is a good time.
> 
> Hope you liked it! If so, gimme a follow on [the Twitters.](http://www.twitter.com/DraceTales)


End file.
